메뉴 건너뛰기




Volumn 46, Issue 10, 2005, Pages 1713-1716

Synthesis of hedychenone, yunnancoronarins and aframodial derivatives

Author keywords

Hedychenone; Labdanes; Natural products; Terpenes

Indexed keywords

AFRAMODIAL; DITERPENE; HEDYCHENONE; UNCLASSIFIED DRUG; YUNNANCORONARIN A; YUNNANCORONARIN D;

EID: 13744252625     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.053     Document Type: Article
Times cited : (17)

References (37)
  • 25
    • 0001317616 scopus 로고
    • The work of S. Proskow on the oxidative degradation of sclareol has remained unpublished but is quoted in: E.J. Corey, and R.R. Sauers J. Am. Chem. Soc. 81 1959 1739 1743
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1739-1743
    • Corey, E.J.1    Sauers, R.R.2
  • 28
    • 0031967318 scopus 로고    scopus 로고
    • Prepared by lithiation (n-BuLi, THF, -78°C, 15 min) of 3-bromofuran, which is expensive but can be prepared; see: G.A. Kraus, and X. Wang Synth. Commun. 28 1998 1093 1096
    • (1998) Synth. Commun. , vol.28 , pp. 1093-1096
    • Kraus, G.A.1    Wang, X.2
  • 29
    • 85030822184 scopus 로고    scopus 로고
    • note
    • 3) δ: 200.8 (CO); 199.4 (CHO); 155.9 (C-8); 128.9 (C-7).
  • 30
    • 85030819396 scopus 로고    scopus 로고
    • note
    • This step was carried out as in Scheme 1 (e.g., 8 to 9) but without purification of the intermediates
  • 32
    • 0002474209 scopus 로고    scopus 로고
    • For a review on biologically active unsaturated 1,4-dialdehydic terpenoids, see: M. Jonassohn, and O. Sterner Trends Org. Chem. 6 1997 23 43
    • (1997) Trends Org. Chem. , vol.6 , pp. 23-43
    • Jonassohn, M.1    Sterner, O.2
  • 35
    • 85030823207 scopus 로고    scopus 로고
    • note
    • This configuration was assigned after observation of a NOE effect between H-11 and H-14
  • 36
    • 0000234498 scopus 로고    scopus 로고
    • IBX/AcOEt was used under the conditions described by: J.D. More, and N.S. Finney Org. Lett. 4 2002 3001 3003 6-keto by-products are obtained but the overall yield of the reaction scheme is fair enough to avoid a protection/deprotection sequence of the secondary hydroxyl group (OH-6)
    • (2002) Org. Lett. , vol.4 , pp. 3001-3003
    • More, J.D.1    Finney, N.S.2
  • 37
    • 0344680113 scopus 로고
    • 3) δ: 198.3 (C-16); 193.3 (C-15); 160.4 (C-12); 133.8 (C-13); 76.0 (C-8); 66.4 (C-6); 62.2 (C-9, C-5); 42.5 (C-7); 40.8 (C-3); 39.4 (C-1); 39.0 (C-10); 35.8 (C-14); 32.3 (C-18); 29.6 (C-4); 25.9 (C-11); 22.4, 21.9 (C-19, C-17); 18.0 (C-2); 16.3 (C-20). For data on aframodial: see: S.F. Kimbu, T.K. Njimi, L. Sondengam, J.A. Akinniyi, and J.D. Connoly J. Chem. Soc., Perkin Trans. 1 1979 1303 1305
    • (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 1303-1305
    • Kimbu, S.F.1    Njimi, T.K.2    Sondengam, L.3    Akinniyi, J.A.4    Connoly, J.D.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.